Methyl Acrylate → (S)-1-Ethyl-2-oxocyclohexanepropanoic Acid Methyl Ester

Participants

Reaction Steps

A solution of (R)-α-methyl-N-(2-ethylcyclohexylidene)-benzenemethanamine (1.303 kg, 5.68 mol), and methyl acrylate (5.68 mol, 489 g, 511 mL) in 2.5 L of dry tetrahydrofuran was sealed under nitrogen and placed in the dark for 21 days. The tetrahydrofuran was then removed on a rotary evaporator and the residue was divided in half. Each half was stirred for 1.5 hours in 3.5 L of 1M hydrochloric acid and extracted with ether (4×700 mL). The extracts were combined, washed with 1M hydrochloric acid (2×500 mL), 1M sodium hydroxide (500 mL) and brine (500 mL). The two halves were combined and concentrated affording 689 g (3.25 mol, 57%) of yellow oil.

Provenance & Evidence